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Biographical notes on War Captains and Mercenary Leaders operating in Italy between 1330 and 1550

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Strategy and Sword: The Remarkable Life of Giovanni degli Ubaldini

Italian CondottieriStrategy and Sword: The Remarkable Life of Giovanni degli Ubaldini

For John Hawkwood (Giovanni Acuto), the finest Italian commander of his time. Friend to the lord of Padua, Francesco Novello da Carrara, so much so that, under the payroll of the lord of Milan, Gian Galeazzo Visconti, he refuses to ride against the Carrara family, preferring instead to be redirected to Tuscany to fight against the Florentines. He dies in Siena, not without suspicion of poison given to him by his rivals in a basket of cherries. His funerary monument in the city's cathedral and the altarpiece that depicted him on horseback were destroyed in 1506 by the lord of Siena, Pandolfo Petrucci.

Indice delle Signorie dei Condottieri: ABCDEFGIJLMNOPQRSTUVZ

The Battles and Triumphs of Giovanni degli Ubaldini.

Giovanni degli Ubaldini, a prominent 14th-century condottiere, fought across Italy, notably against Florence and alongside figures like John Hawkwood and Gian Galeazzo Visconti. Victorious in significant battles and eventually the General Captain of Milan’s troops, he died possibly by poisoning in Siena in 1390 and was honored with a burial in the cathedral.

Giovanni degli Ubaldini/Giovanni d’Azzo degli Ubaldini of Castel Lombardo. Lord of Polenta, Badia di Susinana, and Tirli.

Death: 1390, June

Year, monthState, Comp. venturaOpponentConductActivity AreaActions taken and other salient facts
Oct.Comp. venturaFlorenceTuscanyHe is part of the Company of Saint George of Ambrogio Visconti and John Hawkwood (Giovanni Acuto). In the middle of the month, the Florentines agree to pay the adventurers 6000 florins in exchange for their commitment not to attack the territories of the republic and its allies for four years. The agreement is signed not only by Visconti and Hawkwood (Acuto), but also by Tommaso Merezal, Ugolino Ethon, and 42 other constables.
Dec.UbaldiniFlorenceRomagnaHe assists his brother-in-law Francesco di Dovadola in defending Portico di Romagna, which is attacked by 600 infantrymen. He is declared an outlaw by the Florentines; on Ubaldini, as on all of his family members, a bounty of 1000 florins is placed, to be awarded to his killer.
May – JulyTuscanyHe is besieged in the castle of Badia di Susinana by Obizzo da Montegarulli. The inhabitants revolt at the beginning of July and hand him over to the opponents. Giovanni degli Ubaldini is taken to Florence with a son; he must surrender to the Florentines in the Apennines, under the threat of beheading, the Val d’Agello along with its little fortress and the castle of Tirli. Finally handed over to Obizzo da Montegarulli, he is released by the commander.
…………ChurchFlorenceRomagnaLeading a considerable number of Breton horses, he assists his brother-in-law Francesco di Dovadola in retaking Portico di Romagna, at the expense of the Florentines.
Oct.FermoChurchMarcheAlongside Lucio Lando, Azzo da Castello, and John Hawkwood (l’Acuto), he fights in support of the lords of Fermo (Rinaldo da Monteverde) and Matelica against Rodolfo da Varano.
MayComp. venturaFermo500 cavalryMarcheHe aids the adversaries of Rinaldo da Monteverde. He reaches Sant’Elpidio a Mare and conquers one of the two bastions built to besiege the area. Forty of the enemy’s horses surprise his men, putting them to flight and causing some losses.
Jan.He seizes the castle of Sant’Elpidio a Mare in a swift assault, pillaging it and using it as a logistical base for the raids of his troops.
Apr.Comp. venturaChurchMarcheUrged by the antipope Clement VII, he heads towards the Marche region with Riccardo Ramsey and John Hawkwood (Giovanni Acuto). The adventurers receive several bounties from the Papal cities loyal to Pope Urban VI.
Aug.Comp. venturaFermoMarcheHe reconciles with Rinaldo da Monteverde; he joins him at Montegiorgio with Corrado Lando, supporting him against the inhabitants of Fermo who had expelled the latter from the city.
…………Comp. venturaFanoMarcheHe threatens Galeotto Malatesta in Fano, at the head of the Company of the Star, powerful with 600 lances, all exiles from various Italian states.
…………SienaViterboTuscanyCommanding 2000 cavalry and 1000 infantry, he collaborates with Spinetta Malaspina to the detriment of Francesco di Vico.
MayUmbriaHe is stationed in the territory of Bettona.
JuneComp. venturaFermo, Rimini, CamerinoMarcheTogether with Lucio Lando and Niccolò da Monteverde, he attempts to provide aid to Rinaldo da Monteverde, besieged in Montefalcone Appennino. Upon receiving news of Rinaldo’s capture and execution, Giovanni degli Ubaldini ravages the territory of Fermo. He receives provisions from Rodolfo da Varano and 1500 florins (a bounty) from the people of Fermo. He then departs from the territory with Lucio and Corrado Lando, passing through the counties of Rimini, Pesaro, Fano, Senigallia, and Fossombrone. The Malatesta family grants him an additional 1200 ducats.
July – Aug.ChurchAntipope200 cavalry and 200 infantryUmbriaIn the Orvieto area; he switches to the service of Pope Urban VI against the troops of the antipope Clement VII and those of Rinaldo Orsini. He causes significant damage to the faction of the “muffati/beffati”, seizes Castel di Fiori and the Abbey of Acqua Alta.
Sept.DurazzoNaplesUmbriaHe transfers to the service of Carlo di Durazzo, acting against Giovanna d’Angiò. He moves towards the Perugia area with Giannozzo da Salerno; he is approached by ambassadors of the commune, requesting him to hinder the devastation of the territory.
Oct.UmbriaHe again heads towards the Perugia area with Marsilio da Carrara: he is received by the people of Perugia with all honors, and offers are made to him to switch to the payroll of the commune.
Mar. – MayBanned, Comp. venturaCittà di Castello, RiminiTuscany, Umbria, Romagna, MarcheHe goes to Florence and requests to be employed by the republic. After receiving a negative response, at the end of March, he leaves the area of Arezzo, connects with Giovanni Ordelaffi, and carries out some raids in the countryside of Città di Castello with the exiles. He stops at San Giustino: the militias of Città di Castello defeat the rebels in the area and capture Ugolino del Monte a Santa Maria, son of Piero. Along with Lucio and Corrado Lando, he harasses the counties of Rimini, Pesaro, Fano, and Fossombrone: he is driven away with the payment of substantial bounties.
June – JulySienaComp. ventura720 cavalryTuscany, LazioHe is hired along with Corrado Lando, Corrado di Altinberg, and Il Boino (2000 cavalry and 1000 infantry) for two months by the Sienese to counter the company of Bretons led by Bernardo and Guglielmetto della Sala, which has occupied Montorio. He is granted a monthly salary of 500 florins. He reaches Lucignano where he is handed, as an advance payment, 17000 florins by the commissioners Goro Sansedoni and Giacomo di Pagno; particularly to Ubaldini, an additional 5000 florins are also granted so that he does not disturb the Sienese area before the signing of the agreement. Part of the troops remains in Lucignano in Val di Chiana; with the remaining men, Ubaldini devastates the lands of the Farnese and Baschi families who support the Bretons by supplying them with provisions. He gains control of Marsiliana Castle, negotiates for Sorano Castle from Stefano di Ormanno and for Castell’Ottieri from Giovanni di Pietro; he destroys the fortress of Ponte del Rigo, controlled by the same company. He returns to the territory of the Farnese and extends his raids up to Acquapendente and San Lorenzo. The campaign costs the commune of Siena 17000 florins.
Aug.Comp. venturaSienaTuscanyUpon the expiration of his contract, he wages war against the Sienese; the company disbands. Some members move to the Kingdom of Naples to support the cause of Carlo di Durazzo, while others remain with Ubaldini. The commander stays in the troubled Arezzo area, affected by internal wars; he seizes several castles, such as Gargonza and Palazzuolo, which he then sells back to the Sienese for 4250 florins. He promises not to disturb the Sienese territory for two months.
Nov.Comp. venturaFermo, RiminiMarcheHe passes through Chiaravalle with Lutz Von Landau (Lucio Lando); he roams the territory of Montottone. He reaches Montalto and Rotella, besieges Montottone; at the end of the month, he pillages the village and returns to Chiaravalle due to the resistance encountered.
Apr.TuscanyA conspiracy of his against the Florentines is uncovered in Firenzuola. Several conspirators are hanged; one is beheaded by the Captain of the People of Florence, Obizzo Alidosi.
JulyComp. venturaFermoMarcheHe returns to the Fermo area with Guglielmo Ferrebach and Guglielmo Cogno; he lies in wait near the Girifalco fortress, in a forest called Grifone; he only departs after the payment of a bounty of 2000 florins.
…………ChurchAntipopeUmbriaIn the Orvieto area with Ugolino da Montemarte and Simonetto Orsini; he enters Monteleone d’Orvieto and Montegabbione, from where the da Marsciano are expelled.
Jan.Comp. venturaPerugia, SienaLazio, Umbria, TuscanyHe leaves the countryside of Rome with John Hawkwood and Riccardo Ramsey; he enters the Perugia area; having obtained 15000 florins, he moves into Val di Chiana; he occupies Fabbrica and assaults Buonconvento. The Sienese are aided by the Florentines; the adventurers retreat into the Arezzo area after having left their garrisons in Fabbrica. Ubaldini and his company are given 7000 florins by the Sienese.
MayComp. venturaSienaTuscanyHe returns to the Sienese territory with the company of Bretons and the Company of the Rose; he stays longer in the area until an additional 15000 florins are recognized in his favor.
JuneLazioTogether with the prefect Giovanni di Vico, he defeats the Sienese led by Guido d’Asciano and Niccolò Malatesta at San Lorenzo Nuovo.
JulyTuscanyHe encamps in the countryside of Cortona, reconstitutes the Company of the Rose with John Hawkwood (l’Acuto) and Riccardo Ramsey. He plans to move to Romagna to join forces with Lutz Von Landau (Lucio Lando).
Nov.Comp. venturaUmbria, TuscanyHe is spotted in Assisi. In the church of Santa Maria degli Angeli, he swears a pact of alliance with John Hawkwood (Giovanni Acuto) and Riccardo Ramsey.
Dec.Comp. venturaSiena, Città di CastelloUmbriaThe three commanders roam the Sienese territory. A bounty of 8000 florins (5000 official and 3000 under the table) is delivered to the adventurers. He invades the Tifernate area (Città di Castello) with 2000 cavalry and 1000 infantry: he obtains provisions from Cardinal Galeotto da Pietramala based in Citerna.
Jan.Comp. venturaLuccaTuscanyThreatens Lucca with Riccardo Ramsey.
MayComp. venturaSiena, Pisa, Lucca, Ascoli PicenoTuscany, MarcheHe moves near Cortona; from here, he threatens all of Tuscany with Acuto and Ramsey: the Sienese recognize the three captains with 7000 florins, provide them with supplies, and grant passage to their troops; the Pisans acknowledge them with 9000 florins, and the Lucchesi with an additional 4000. Giovanni degli Ubaldini relocates to the Marche of Ancona; he reaches Fermo with Acuto; crosses the territory of Montegiorgio, and, following the delivery of 1000 florins each for the two captains, the mercenaries plunder Ascoli. Ubaldini positions himself above Castignano, passes the plains of the Tenna, and sets up camp in Sant’Elpidio a Mare. He is supplied with provisions by the local inhabitants.
JunePerugiaBannedUmbriaHe stops at Mantignana; there, he is hired along with the other two captains for fifteen days with the aim of bringing the Michelotti, assisted by Boldrino da Panicale, into obedience. He is tasked with reclaiming the islands in Lake Trasimeno that have fallen under the control of the adversaries. However, his action yields no effect.
JulyVicoChurchHe battles against the Papal forces with Acuto and the troops of Prefect Francesco di Vico.
Aug.TuscanyHe offers himself to the Florentines to counteract the march of Enguerrand de Coucy.
Sept.AnjouArezzoTuscanyHe connects with Acuto, Enguerrand de Coucy, Gaspare degli Ubaldini, and the exiles from Arezzo led by the Pietramala. With them, he enters the city under the cover of night. Also, in the area, there is the sudden arrival of Alberico da Barbiano, summoned hastily by Perugia. There are several clashes over three days, at the end of which Enguerrand de Coucy emerges as the dominant figure in the situation.
Nov.Comp. venturaSienaTuscanyWith the death of Luigi d’Angiò, Enguerrand de Coucy sells Arezzo to the Florentines for 50,000 florins, despite the resistance of the Ghibellines and the exiles. Giovanni degli Ubaldini leaves the area and, along with Riccardo Ramsey, Acuto, Corrado Lando, and Rinaldo Orsini, heads towards Anghiari and Borgo San Sepolcro (Sansepolcro) to the detriment of the Sienese. The usual depredations relentlessly follow.
Dec.ApuliaHe continues his march with Riccardo Ramsey towards Apulia.
Jan.EmiliaHe is led by the Sienese to confront Farnese, Tolomei, and Salimbeni in exchange for the plundering of their possessions for two days. Blocked at the passes of the Bolognese Apennines towards Tuscany, he is forced to turn back.
Feb.Comp. venturaFerrara, Bologna, FirenzeEmiliaHe stops in the Modenese area and then moves to Romagna. He forms an alliance with Giovanni da Barbiano to fight against the Estensi and arrives at San Prospero. When attacked by the adversaries, who are reinforced by Florentine and Bolognese militias, he routs them and forces them to seek refuge in Castel San Pietro Terme.
Apr.RomagnaGiovanni da Barbiano returns Zagonara to the Estensi, and Ubaldini departs from Barbiano with his company. In the same month, along with Acuto, Taddeo Pepoli, Everardo della Campana, and Boldrino da Panicale, he forms a new company called the Company of the Rose, consisting of 3000 cavalry and 1000 infantry, comprising both Italians and Germans.
JuneComp. venturaBologna, MilanRomagna, Emilia, LombardyHe leaves Romagna and, along with the other condottieri of the company, focuses on Lombardy. Their objective is the liberation of Bernabò Visconti from the prison in which he has been confined by his nephew Gian Galeazzo. The Bolognese attempt in vain to obstruct their passage; Ubaldini devastates their territory and obtains a delivery of 30,000/35,000 florins (officially stated as 15,000). After reaching a settlement, he returns the hostages and continues peacefully on his march. The mercenaries are soon blocked by the Visconti forces, leading to a separation among the condottieri. Ubaldini heads towards Tuscany and enters the territory of Cortona with Acuto and Enguerrand de Coucy. He approaches Cortona, claiming to defend the rights of Francesco Senese and Aloigi Casali, both descendants of Bartolomea degli Ubaldini. Beatrice Castracani, the mother of the lord of Cortona, Uguccione Casali, who is the daughter of Francesco, contacts the condottiero through her advisor Carlo Castracani. Ubaldini only departs from the territory after the solemn celebration of the marriage between his sister Tancia and Andrea Casali, the uncle of the local lord Uguccione.
JulyComp. venturaFlorenceEmilia, UmbriaHe is in Cavezzo in the Modenese region, and the Florentines provide him with 10,000 florins to refrain from entering Tuscany. He then returns to the Perugian region.
Sept.PaduaVerona, Venice2000 cavalryVeneto, FriuliHe meets with the Patriarch of Aquileia, Filippo di Alençon, in Treviso and then proceeds to Friuli to counter the Venetians and the Scaligeri. He secures Portogruaro from Rizzardo da Valvasone, captures the castle of San Vito al Tagliamento, occupies Spilimbergo and Savorgnano, despite the resistance of the Venetians. He besieges Udine and plunders its territory.
Oct.General captainFriuliHe is reported to be near San Daniele del Friuli; however, he faces difficulties due to heavy rains and inadequate supplies. He crosses the Tagliamento, losing many men who drown while attempting to ford the river. He halts for a few days between Zoppola and Castiglione, sets fire to Maniago, and unsuccessfully besieges the castle there.
Feb.VenetoHe moves against the Scaliger territory with Cermisone da Parma, who commands 2000 provisioned troops; he overcomes the resistance at Ponte di Barbarano of the militias led by Cortesia da Serego and Benedetto da Malcesine; he raids the borderlands along the Brenta. Many are taken prisoner; the heads of livestock seized are driven to Padova.
Mar.VenetoHe still confronts Cortesia da Serego in the territory of Montegalda.
JuneVenetoAn adept maneuver by Cortesia da Serego at Brentelle diverts the Paduan troops led by Giacomo da Carrara, thus allowing the core of the Scaliger army to break through the defenses near Brusegana and push almost to the walls of Padova. Upon hearing the news, Ubaldini leaves Rovolon and moves to Tencarola: he sends Ceccolo Broglia with 100 lances on a scouting mission to spy on the Scaliger encampments and seek a skirmish. Since Serego is already under Padova, he positions himself at Maddalene, outside Porta di Santa Croce. By evening, the Scaligers’ success seems certain; the Veronese soldiers disperse to engage in looting. Ubaldini restores the situation; by the first light of the following day, his troops are reorganized, bolstered also by citizens and peasants from the territory. Cortesia da Serego sends the squads of Facino Cane and Francesco da Sassuolo to attack, who rout the Carraresi and start chasing them; the rest of the Scaliger army gives in to plundering and disperses across the countryside. Ubaldini realizes that Serego is left with few troops at his disposal; he orders Pagano da Rho and Giacomo da Carrara to attack the rear of the opponents who are tailing the Paduans fleeing towards the city. He also arranges for Antonio Pio (who raises the standard of the Carro) and, especially, Cermisone da Parma to join him with 1800 infantrymen for the final attack on the opponents. He thus catches the Scaligers in a full crisis of movement, disorganized; with a mighty assault in less than two hours, he overwhelms all resistance and captures the main enemy commanders including Cortesia da Serego, Facino Cane, Ostasio da Polenta, Giovanni Ordelaffi, and Ugolino dal Verme. In the battle, out of 10000 fighters, 7910 are taken prisoner (4460 infantry and cavalry, and 3450 men of lower status); there are 821 deaths; included in the count are also those who drowned trying to flee capture. The Paduans also capture 120 merchants with 240 carts of provisions; the prostitutes found at the camp (211) are also brought to Padova to be welcomed with great festivities; finally, the Carraresi gain possession of 52 bombards both large and small, 172 trebuchets, and 6350 mounts. The soldiers are granted double pay and a full month’s salary. Ubaldini is knighted by Pagano da Rho: the lord of Padova, Francesco da Carrara, goes to Porta Savonarola to honor him.
Aug. – Sept.Comp. venturaFlorenceVeneto, Romagna, MarcheHe conquers the bastion of Rovolon and storms the towers of Longare in the Vicentine area. He then moves to Romagna; he joins forces with l’Acuto and Giovanni Tedesco da Pietramala, and with them, he moves to assist Antonio da Montefeltro, with whom he is bound by friendship and kinship ties. With his mere presence, within eight days, he compels the Florentines to reach an agreement with the lord of Urbino.
Oct.PaduaVeronaVenetoThe conflict with the Scaligers resumes, now under the command of Lucio Lando. A diversionary action in the Veronese territory leads him to return to Padova laden with prisoners and livestock.
Nov.VenetoHe allies with Gian Galeazzo Visconti through a treaty that obligates him to timely unite into a single company forces that are fighting both for the Carraresi and the Scaligers: the Count of Virtù (Gian Galeazzo) seemingly lends him a sum of 12000 florins. Ubaldini leaves Padova with 1000 lances to aid the towers of Novaglia (a strategic point for controlling the water regime of the territory) besieged by Lucio Lando. In the dead of night, he arrives at Longare and has a vessel launched into the Bacchiglione. With the first journey, three carts loaded with large crossbow bolts, gunpowder for bombard cannons, and other weapons are delivered to the defenders of the towers; this supply is followed by a second dispatch, still unnoticed by the Scaligers, consisting of 50 infantrymen.
Dec.Veneto, RomagnaTaking advantage of an unusually harsh cold, he travels to Faenza to enlist under the Carraresi’s pay l’Acuto (500 lances) and Giovanni Tedesco da Pietramala (1000 horses). Voluntarily, he yields the command of the troops to the English condottiero.
Jan.VenetoHe moves into the Veronese territory with Francesco Novello da Carrara; he secures passage through Estensi territory at Carmignano di Brenta, arrives at Castelbaldo, and overcomes the resistance of Giovanni Ordelaffi at Fossa Imperiale, then bursts into the Veronese region.
Feb.VenetoInformed that l’Acuto has also crossed the Adige, he sends Bernardo Scolari to meet him; he connects with the English condottiero at Cerea. At the war council held with Francesco da Carrara, also present are Ceccolo Broglia, Giovanni Tedesco da Pietramala, Ugolotto Biancardo, Bernardo Scolari, Conte da Carrara, Filippo da Pisa, Antonio Balestrazzo, and Antonio Lupo. On this occasion, he officially resigns the position of general captain and entrusts it to l’Acuto. The decision is made to target Verona to plunder the territories of Bussolengo and Cavaion Veronese; with l’Acuto, he aims to seize the bridge of Bussolengo in order to penetrate into Valpolicella: he is dissuaded from this by Scolari. The camp lacks provisions. For twenty days, the soldiers have no bread or meat; they are forced to subsist on legumes and turnips; some, in order to feed themselves, kill their own mounts. Often the soldiers disperse in search of provisions.
Mar.VenetoHe retreats to Castelbaldo, where a new council of war is held. The Scaligers, under the command of Ordelaffi, decide to attack the Carraresi: before the battle, Ubaldini with l’Acuto knights Conte da Carrara and Bernardo Scolari. In the battle, he commands the second squadron of 1000 horses with Giovanni Tedesco da Pietramala, Filippo da Pisa, and Borso Gambara. He clashes with the Count of Anchre; he repels, with Antonio Balestrazzo and Filippo da Pisa, the first enemy squadrons that have crossed the ditch. At the end of the day, among the Scaligers, there are 716 dead, 846 wounded, and 4620 prisoners including Ordelaffi, Ostasio da Polenta, and Benedetto da Malcesine. Days later, he returns to Padova with the prisoners and is welcomed at the gate by the lord of the city who, in the evening, invites all the condottieri, both victors and vanquished, to dinner.
Apr.MilanVerona350 lancesVenetoHe returns to the Veronese through Monselice and Montagnana; with l’Acuto and Francesco Novello da Carrara, he forcefully overcomes the barricades of Villanova and Soave, arrives at Verona at Porta Vescovo, and sets fire to all the villages found along the way up to Montorio Veronese. After a week, he returns to Padova laden with spoils and loot. In the same month, he is granted permission to serve the Visconti to continue fighting the Scaligers.
…………LombardyHe is at the camp of Desenzano del Garda where 7000 ducats are delivered to him by two members of the household of the Count of Virtù. The Marquis of Este and Francesco Gonzaga grant him passage.
July – Oct.General captainVeneto, LombardyHe assaults the castles around Lake Garda; almost without resistance, Peschiera del Garda, Bardolino, Garda, Castione Veronese, Brenzone, Torri, Rivoli, and Malcesine fall into his hands. Only Lazise fights for six days and is sacked by his men in mid-October. The first to enter the city is the artillery commander Giovanni Zinchero, followed by Spinetta Malaspina. Gian Galeazzo Visconti appoints him general captain. The ceremony takes place in Milan at the Church of Sant’Ambrogio. Ubaldini then goes to Brescia, gathers 6000 men, crosses the Mincio, and positions himself near Valeggio where he is also joined by some squads sent by the Carraresi. In Verona, confusion and dismay spread; some secretly prepare to hand over the city to the Visconti. Veronese exiles such as Guglielmo Bevilacqua, Antonio and Spinetta Malaspina, Antonio Nogarola reach Ubaldini‘s camp. Bevilacqua promises 5000 ducats and a command of 150 infantrymen to a constable of Porta San Massimo, named Correggiotto da Piacenza, if he finds the gate open for him. Bevilacqua, with 300 infantrymen, approaches the walls, the drawbridge is lowered, and there are no more obstacles to his entry into the city. According to Milanese sources, it is some of Ubaldini‘s men-at-arms who penetrate the borough after pretending to be prisoners of some citizens; they seize the gate, kill the captain and the sentinels, and open it to let the rest of the Visconti army enter. The first to enter the city is the artillery commander Giovanni Zinchero, immediately followed by Spinetta Malaspina.
Nov. – Dec.Comp. venturaBologna, Forlì, Ravenna, RiminiVeneto, Emilia, RomagnaHe meets with Francesco Novello da Carrara at Codevigo and moves to the Modenese area with 1500 lances; his presence interrupts the sowing activities in the fields. Florence sends 300 lances and 500 crossbowmen to aid the Bolognese, while the Sienese promise him 6000 florins to spare their territory from the raids of his company. In December, the Bolognese also recognize him 15000 florins. The Florentines, for their part, absolve him and his sons from all bans; in fact, a yearly provision of 1800 florins is promised to him for a decade. He heads to Romagna, to Oriolo (Oriolo dei Fichi), to facilitate Giovanni Ordelaffi who wishes to take control of Forlì at the expense of his relatives Pino and Cecco. Some assaults by his militias on Fiumana and Rocca delle Caminate are repelled; he seizes more castles in the Cesenate and Ravennate areas (14, including Lugarara, Casalbuono, Polenta, and Coglianello), either by force or by negotiation. Guido da Polenta urges him against Carlo and Pandolfo Malatesta; he is blocked at Cervia by the latter. At Bertinoro, he quarrels with Ordelaffi who, having changed his mind, prefers to serve under the Malatesta. This leads to a violent dispute between the two condottieri; Ubaldini accuses Ordelaffi of treason also because he has kept 4000 florins belonging to him. Because of this division, he is now also attacked by the Bolognese.
Jan.The Sienese deliver 5000 florins to him.
Mar.RomagnaHe retreats to the Ravennate with the permission of Guido da Polenta; his company begins to disintegrate. He reaches Forlì to negotiate peace with the mediation of the Visconti; the negotiations bear no fruit. At the same time, some castles in Tuscany rebel against him; the Florentines promptly commit to their recovery.
MayRomagnaHe reaches an agreement with the Malatesta, retaining control of the castles of Coglianello and Polenta; at the end of the month, he joins forces with Pandolfo Malatesta and Bartolomeo da Pietramala, planning to advance into Tuscany without regard for the convention signed just a few months earlier.
JuneTuscanyHe is contacted by the Florentines who offer him the command of 300 lances for a month to fight Jacopo d’Appiano in Pisan territory; however, the initiative does not materialize.
…………He is ordered by the Visconti to ride into Paduan territory against the Carraresi, but he refuses due to the friendship that binds him to Francesco da Carrara. He is then diverted towards Tuscany with 1000 lances; this army includes many from Siena, Perugia, the Tarlati, and other Tuscan exiles. In November, Francesco Novello da Carrara surrenders at the discretion of the Visconti and requests his support.
…………In the Bolognese area.
Mar.He arrives in Siena; he secretly sends his agent, Jacopo di Montepulciano, to Florence, who is discovered and arrested on charges of plotting in favor of the Visconti.
Sept.Ever restless, he has his constable Giovanni Piccinino di Vallereno approach Ugolino da Panico to incite rebellion in the Bolognese mountains against the commune of Bologna.
Oct.Gian Galeazzo Visconti and the Florentines conclude a sort of alliance treaty.
Feb.Umbria, TuscanyHe is noted in Perugia and Siena for seeking treatment at the local baths. The authorities welcome him with all honors and present him with gifts of confections, wines, wax, forage; a multi-course lunch is offered to him and his men.
Apr.SienaFlorenceTuscanyHe leaves Siena with 300 lances; joining him in his expedition against the Florentines are various condottieri such as Ceccolo Broglia, Brandolino Brandolini, Cristoforo di Santa Fiora, Cocco Salimbeni, and Giovanni Tedesco da Pietramala. The Florentines consider him ungrateful for the favors bestowed upon him and the provision granted to him; they sentence him to death. He heads to Val d’Ambra, secures 6 castles through negotiations (100 prisoners; much livestock is driven to Siena for the occasion). He continues his advance and, through his chancellor, the Dominican friar Antonio da Castel San Giovanni, negotiates a treaty with Giampaolo Ricasoli to obtain Castel San Giovanni (San Giovanni Valdarno). Leaving Siena under cover of night, he enters Valdarno and presents himself before the walls, expecting to find a gate open as per the agreements. The inhabitants resist the betrayal. Ubaldini is forced to retreat to Leona and Siena. For their demonstrated loyalty, the citizens are exempted from certain taxes for thirty years.
MayMilanFlorenceTuscanyVisconti officially declares war on the Florentines; Giovanni degli Ubaldini once again leaves Siena with 500 horses through Porta Ovile; he captures 110 men in three ambushes at Camposervoli, turns to Val di Chiana, and assaults the castle of Lucignano, with Giovanni Tedesco da Pietramala being the first to enter. He returns to Siena; 30 Guelphs place a bounty of 10000 florins on his head; he in turn offers 2000 florins for the death of anyone on that list. On the day of Ascension, he leaves the city with 3000 horses, 4000 infantry, including many crossbowmen and about 800 sappers: he positions himself near Montepulciano, causing severe damage to the countryside and places near the walls. The area is about to surrender when the Florentines sack the Val di Strove. He moves to confront them and finds that the opponents have already departed. Repelled from the castle of Foiano della Chiana, he moves to Val d’Ambra where San Pancrazio surrenders to him (capturing 30 infantry). Soon after, he takes Palazzuolo, Gargonza, Bucine, Capannole, Badia a Ruoti, Cennina; he approaches Arezzo, storms, and plunders Battifolle. He stays with Giovanni Tedesco da Pietramala for several days under the walls of the provincial capital, seizes another 6 castles belonging to the Tarlati when he is recalled to the Sienese area. He forces the Florentines to retreat to Val d’Elsa, plunders the countryside of Volterra, and sacks several small castles.
JuneTuscanyIn Siena, he attends the ceremony where the inhabitants of Lucignano submit to the commune. He resumes operations in Chianti; he heads to the castle of San Giusto alle Monache, from where the Florentines had conducted numerous raids into Sienese territory. He loses many men in several assaults. He procures 2 bombards from Siena (the first used in Tuscany) and after a few shots (stones of 300 pounds), the defenders surrender on terms. The castle is sacked and destroyed from its foundations. Falling ill in the camp, he returns to Siena for treatment. He dies at the end of the month in the city, not without suspicion of poison administered by the Florentines in a basket of cherries. Amid a mourning city with closed shops, his body is carried on a bier surrounded by golden torches lined with vair fur, adorned with a cloth of gold and other precious fabrics. It is escorted by 36 horses covered in silk and ridden by knights with banners, armed with swords, wearing helmets with their crests and spurs. Behind them, 400 people, all dressed in brown and part of his company, march. 800 torches and more than 500 double torches, mounted on poles, honor the condottiero. The city’s Signoria is fully present; the funeral procession is finally followed by 15000 people. The body is taken to the cathedral; the mass is concelebrated by the Bishop of Siena and the Abbot of San Galgano. Ubaldini is buried near the altar of San Savino. The funeral costs the commune a total of 3000 florins, to which another 2000 florins must be added for burial expenses. His tomb will be moved from the cathedral in 1404 along with that of Giovanni Tedesco da Pietramala. The altarpiece, representing the condottiero on horseback, will instead be placed behind the main door of the church, only to be destroyed in 1506 by the Lord of Siena, Pandolfo Petrucci. Giovanni degli Ubaldini is remembered alongside Giovanni Acuto in the novel “The Wandering Knight,” a work by the Marquis of Saluzzo, Tommaso III. A street in Padova is dedicated to him.


-“Primo tra ‘primi per tempo e per valore fu certamente Giovanni d’Azzo degli Ubaldini, rampollo di que’ forti vassalli, che salvaticando nelle aspre castella degli Apenninni, erano stato per lunga pezza guida o terrore delle città vicine. Arrivava la costui brigata a 2000 cavalli e 1000 fanti italiani, tedeschi, brettoni d’ogni razza e costume.. Capitano il più sperimentato dei sui dì, per testimonianza del medesimo Acuto.” RICOTTI

-“Morte molto dannosa a’ suoi, essendo l’Ubaldini tenuto per uomo valoroso di sua persona, per intendentissimo dell’arte militare e ..fidatissimo alla parte.” AMMIRATO

-“Maestro di guerra.” MURATORI

-“Di lui fece le più ampie lodi lo stesso Acuto che lo aveva sempre tenuto in gran concetto.” ARGEGNI

-“Aveva acquistato grande potenza e fama nell’arte militare.” L. ARETINO

-“Celebre nella scuola della Milizia italiana.” CANESTRINI

-“Capitano di Nobilissima Stirpe, degno di somme lodi, peritissimo nell’arte militare, e pratichissimo sopra tutti gli altri, che furon al tempo suo.” MALAVOLTI

-“Era costui il migliore conducitore di gente d’arme ch’avesse Italia e veramente valente uomo; e per la morte di lui rimase la gente del Conte (Gian Galeazzo Visconti) sanza capitano valente, e molto, sbigottiro tutti gli altri suoi soldati.” MINERBETTI


“Rei militaris peritia clarus.” BIONDO

-“Onorevole famoxo homo..Era di lialli cavalieri e proveduto e prò e sagacie in fatti d’arme ch’a quei giorni s’acatasse.” GATARI

-“Huomo scaltro e avvezzato nel mestiero dell’armi.” SARAINA

-“Maestro di guerra.” LANCETTI

-“Valente capitano.” PAGANO

-“Che in virtù militare si paragonava all’Auguto.” PIGNOTTI

-“Egregium ea tempestate belli ducem..Vir nobilitate gentis clarus, et scientia rei militaris suae aetatis peritissimus, ut qui ab Auguto caeteris Italiae ducibus prudentia et bellicis artibus praeferretur.” BRACCIOLINI

-“Ubaldinum Johannem, stirpe magnifica natum, disciplina preditum militari, in celorum Regine templo Senarum urbe, in pauperis ac miserande fortis hospicio, marmora porrigiunt.” MARZAGAIA

-“Di nobilissima stirpe e degno di somma lode per essere stato peritissimo nell’arte militare e prudentissimo sopra tutti gli altri che furono al tempo suo secondo il giudizio di Giovanni Aguto..Di lui e di Giovanni Aguto fa menzione il vescovo di Foligno nel suo quadriregio dove dice: “Dite a Giovanni Aguto il nostro affanno,/ Et a Gio: d’Azzo agli altri compagnoni,/ Che per centauri su nel mondo stanno,/ che la lor condotta gli fu prigione.”.” GAMURRINI

-“Prode capitano di quel tempo.” DE STEFANI

-“Qui erat praecipuus belli dux.” SANT’ANTONINO

-“Capitanio famoxo..e fortissimamente operado in multi grandi fatti,” G. DI M. PEDRINO

-“Fiero Ghibellino.” PEZZANA

-Con Giovanni Ordelaffi “Horum uterque ea tempestate optimi belli duces habebantur.” BUONINCONTRI

-Con Giovanni Tedesco da Pietramala “Ambo armis exercitati, et viri bello praestantes.” BUONINCONTRI

-Con Lucio Lando “Uomini di ventura usi alle rapine.” A. MARINI

-“Il più famoso capitano italiano del secolo XIV, prima di Alberico da Barbiano.” FRANCESCHINI

-“An able soldier and a pleasant fellow.” TREASE

-“Rural lord, whose family controlled a northern access into Florentine territory…Famous Italian mercenary..An excellent soldier, who would forge a close relationship with John Hawkwood.” CAFERRO

-“Ora desidera l’anima mia che mutiate modo, e che pigliate il soldo e la croce di Cristo Crocifisso, e tutti i vostri seguaci e compagni; sì che siate una compagnia di Gesù, ad andar contra a’ cani infedeli che possiedono il nostro Luogo santo, dovve si riposò e sostenne la prima dolce Verità, morte e pene per noi.” Dalle lettere di SANTA CATERINA DA SIENA

-“Who was described by a Florentine diarist as “horrible beyond measure.”” STONOR SAUNDERS

-“Sulle orme di Alberico da Barbiano si muove Giovanni di Azzo degli Ubaldini, che raccoglie una masnada di bretoni, italiani, tedeschi e altri sbandati di precedenti compagnie di ventura.” ADAR

-“Capitano di buona fama.” PAMPALONI

-“Qui ex ea familia (gli Ubaldini) reliquus, militiae dedita opera, famam ingentem ac potentiam sibi comparaverat, et tunc magni dux belli.” BRUNI

-Con Giovanni Tedesco da Pietramala “Duces vero equitatus..Erant vero ambo praestantes belli viri amboque florentini populi inimici.” BRUNI

-Da una poesia scritta in occasione della sconfitta dei bolognesi nello scontro di San Prospero “Difesa non può far più Barbiano,/Zoanne d’Azzo, né ancor Zagonara;/ Che i Bolognesi con quel da Ferrara/Non li convinca con la spada in man/Che Conte, né Soldato, né Villano,/Che li sta dentro, uscir non può che para,/E la passiva ch’é sì forte cara,/Ch’in pochi dì di fame cacherano…” GRIFFONI

Featured image: wikimedia

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Roberto Damiani
Roberto Damiani
Roberto Damiani è l'autore del sito Condottieri di ventura.